Podcast Summary: How to Operate and Scale a Business the Right Way

The GaryVee Audio Experience | October 1, 2025

Host: Gary Vaynerchuk
Guest: Henry Ward, Co-founder & CEO of Carta

Episode Overview

In this episode, Gary Vaynerchuk sits down with Henry Ward, the co-founder and CEO of Carta, for a candid, “meat and potatoes” discussion on the realities of operating and scaling a business. Both leaders share war stories, tactical insights, and philosophy from building companies that have achieved massive scale and longevity. The episode is rich with specific, actionable advice for entrepreneurs, startup employees, middle managers, and anyone who aspires to lead in the business world.

Key Discussion Points & Insights

1. Origin Stories and Building Real Businesses

• The Carta Journey:

  • Henry describes how Carta started in 2013 by digitizing paper stock certificates that were still being physically mailed. Their vision was to "dematerialize equity" much like PayPal did for cash.
    • “Can we do something like what PayPal did for cash?... Could we send equity through email the way PayPal sends money through email?” – Henry Ward (04:05)
  • Early challenges included convincing founders to buy something they didn’t even know they needed: cap table software.

• Moment of Product-Market Fit:

  • The first $120 paid from a customer in 2014 was a pivotal psychological win.
    • “The first time you build something as an entrepreneur that somebody pays you for is a magical moment. I'll never forget it.” – Henry Ward (06:41)
  • Scaling pains: At one point, demand outstripped Carta’s ability to on-board customers, forcing Henry to halt sales to maintain quality.
    • “We had to stop selling ... because our customers are furious because they bought, but we can't deliver.” – Henry Ward (10:33)

2. Scaling Pains: Over-Promising, Under-Delivering, and Customer Trust

• Balancing Growth and Service:

  • Both hosts reflect on the challenge of growing too quickly and the importance of protecting customer happiness.
    • “If people aren’t happy, it kills everything. And I’m willing to take a three-month closing the doors on sales to make sure that’s always true.” – Henry Ward (13:30)
  • Word-of-mouth references became the most important marketing channel—making customer happiness the first priority.

• Two Paths: Fix While Flying vs. Pause and Repair:

  • Gary and Henry discuss different strategies for dealing with scaling gone awry: Either grit through and fix problems on the fly, or—like Henry—pause sales and fix foundational issues.

3. Managing Boards and Investors

• Engagement Tactics:
  • “Adopt a Business Unit” – Henry had each board member work closely with specific business units for better understanding and buy-in.
    • “They helped scale me in terms of the strategy and sort of influencing the organization.” – Henry Ward (15:08)
  • No Surprises Policy: Never surprise your board; consistent, transparent communication preserves trust and your position as CEO.
    • “The number one rule on boards is don't surprise them. Like, that's just it.” – Henry Ward (16:13)
    • “Let me give you the preview: we're going to see you in 90 days and you're going to... have to admit to the problem... they’re going to be pissed.” – Gary Vee (17:29)
  • Previewing bad news with board members before meetings – even one-on-one—ensures smoother board meetings and no trust breakdowns.

4. Leadership Growth and Radical (Kind) Candor

• Gary’s Struggle with Candor:

  • Gary admits candor was his kryptonite as an early leader, sharing that he’s gotten much better at difficult conversations (20:01).

• Henry’s Approach:

  • He distinguishes between "radical" and “kind” candor, emphasizing empathy, context, and curiosity.
    • “Everything I know about people is know your audience... how you talk to them matters.” – Henry Ward (20:25)
    • When giving feedback: Start with curiosity about the employee’s own self-assessment before doubling down on criticism.
    • “The question to solve is, why are you seeing the same thing differently?” – Henry Ward (22:15)

5. Advice for Middle Managers & Organization Building

• How to Stand Out:
  • Middle managers are too often judged by their worst mistake—better organizations recognize and reward their best contributions.
    • “I hope at Carta, we measure middle managers on the best things they’ve done... if that’s true, that means we forgive mistakes.” – Henry Ward (29:11)
  • Recognize the political risk for middle management who shine, and the need for companies to protect and reward upward momentum.

6. Operating at Scale: Eyes and Ears in Large Organizations

• Trusted Insiders:

  • As companies scale, CEOs rely on a network of “family members” for candid, on-the-ground insight beyond formal channels.
    • “Make as many family members as you can... Remember, to be a family member—that requires you putting in the work.” – Gary Vee (34:12)
  • Both Gary and Henry share how many such trusted confidantes they have according to their own company scale.

• Founder CEO vs. Professional CEO:

  • Executives with founder CEO experience adapt better to the dynamic, demanding style founders bring; switching from founder to professional CEO is a watershed moment for any organization.
    • “We've had terrible success bringing executives in that have never worked for a founder CEO before—then they work for me and they just think I’m a maniac.” – Henry Ward (35:45)

7. On Ownership and the Future of Work

• Ownership vs. Payroll:
  • Henry observes a macro shift from selling time for money (payroll) to an ownership era where equity (or analogs) in work is normalized—even beyond tech.
    • “The future of labor is really going to be an ownership era... can we start catalyzing more companies thinking about ownership and employee ownership as a way of compensation?” – Henry Ward (37:45)
• The Enabler: Blockchain
  • Gary connects this vision to blockchain technology, emphasizing its power to enable and authenticate widespread, decentralized ownership.

Notable Quotes & Memorable Moments

• On early validation:
  “The first time you build something as an entrepreneur that somebody pays you for is a magical moment. I’ll never forget it.”
  — Henry Ward (06:41)

• On founder mindset:
  “When you love the game, like, I don’t think a lot of people can actually talk about the first thing they sold... I can remember the first wine I sold for my dad, the first client VaynerMedia had—all of it, like, vividly.”
  — Gary Vaynerchuk (07:06)

• Operational discipline:
  "You have to make sure that the reference checks go well. And if people aren’t happy, it kills everything... willing to take a three-month closing the doors on sales to make sure that’s always true." — Henry Ward (13:30)

• Board management wisdom:
  “The number one rule on boards is don’t surprise them. As long as you never surprise the board, you’ll be okay.”
  — Henry Ward (16:13)

• Candor and empathy:
  “I call it kind candor at VaynerMedia because I think radical people feel like, oh, let me give you the purest form of it, which I actually think seeps into people’s real struggle with candor...”
  — Gary Vaynerchuk (21:02)

• On feedback:
  “What matters is what the employee thinks... If they’re like, I don’t think I’m doing great either, you’re like, amazing. So let’s talk about how I can help... If the employee’s like, I’m crushing it. I don’t know what you’re talking about, that’s a very different conversation.”
  — Henry Ward (22:10)

• Scaling and organizational clarity:
  “There’s this kind of inflection point where I used to be able to keep the whole company in my head... and then you get to the scale you’re at, Gary, and like things just start happening and you’re like, why are these things happening?”
  — Henry Ward (31:21)

• On the difference of founder-led companies:
  “There’s nothing is a bigger change in the history of an organization that’s destined to be big than the day the founder CEO leaves. Nothing is a bigger day. That’s how different it is in the history of the company.”
  — Gary Vaynerchuk (35:14)

Timestamps for Important Segments

• 00:00–02:48: Introduction & guest welcome
• 02:48–05:08: Carta’s purpose, evolution, and digitizing paperwork
• 05:08–08:16: Early product-market fit, validation and first customers
• 08:16–10:53: Scaling issues and halting sales to maintain service
• 12:33–14:47: Over-promising, under-delivering, rectifying with customer experience focus
• 14:47–19:35: Leveraging boards, communication tactics, and board management
• 19:35–23:10: Leadership lessons; candor, feedback, and managing teams
• 27:39–31:11: Advice for middle managers to rise in organizations
• 31:21–34:28: Building internal “family member” networks for scale
• 35:14–36:15: Founder CEO dynamics vs. professional CEO
• 37:13–38:45: The coming era of ownership and the future of work
• 38:46–End: Closing thoughts and final plugs

Final Takeaways

• Operate for the long-term: Ground your business in sustainable practices, not growth at all costs.
• Customer reference is king: Success hinges on happy customers who refer you.
• Proactive communication with boards and teams: Over-communicate, never surprise, and bring empathy to all interactions.
• Enable upward mobility and real ownership: Build environments where real merit is recognized and ownership is possible, for everyone.

Where to learn more: carta.com

This episode provides a masterclass on real-world entrepreneurship, scaling, and leadership from two operators who are in the trenches and unafraid to talk about mistakes and learnings. Whether you’re a seasoned executive, rising manager, or aspiring founder, you’ll find actionable wisdom in every segment.